Information on EC 4.2.1.B20 - onoceroid synthase

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The expected taxonomic range for this enzyme is: Bacillus megaterium

EC NUMBER
COMMENTARY hide
4.2.1.B20
preliminary BRENDA-supplied EC number
RECOMMENDED NAME
GeneOntology No.
onoceroid synthase
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ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
metabolism
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onoceroids are triterpenoids biosynthesized from squalene or (3S)-2,3-oxidosqualene by cyclization from both termini
SUBSTRATE
PRODUCT                       
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
3-deoxyachilleol A
(+)-ambrein
show the reaction diagram
-
from squalene
-
-
?
8alpha-hydroxypolypoda-13,17,21-triene
onoceranoxide + ((1R,2R,4aS,8aS)-2,5,5,8a-tetramethyl-1-{2-[(1S,4aS,8aS)-5,5,8a-trimethyl-2-methylidenedecahydronaphthalen-1-yl]ethyl}decahydronaphthalen-2-ol
show the reaction diagram
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the enzyme constructs the 6/6/6/6-tetracyclic scaffold baciterpenol A from the head-to-tail monocyclic tetraprenyl-betacurcumene as sesquarterpene cyclase, EC 4.2.1.137, and it also forms the 6/6/7/6/6-pentacyclic onoceranoxide and the 6/6 + 6/6-tetracyclic (1R,2R,4aS,8aS)-2,5,5,8a-tetramethyl-1-[2-[(1S,4aS,8aS)-5,5,8a-trimethyl-2-methylidenedecahydronaphthalen-1-yl]ethyl]decahydron from the tail-to-tail acyclic triterpene squalene via the 6/6-bicyclic intermediate 8alpha-hydroxypolypoda-13,17,21-triene
ratio 64:36
-
?
squalene
8alpha-hydroxypolypoda-13,17,21-triene
show the reaction diagram
-
-
intermediate product
-
?
additional information
?
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NATURAL SUBSTRATES
NATURAL PRODUCTS
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
REVERSIBILITY
r=reversible
ir=irreversible
?=not specified
3-deoxyachilleol A
(+)-ambrein
show the reaction diagram
-
from squalene
-
-
?
8alpha-hydroxypolypoda-13,17,21-triene
onoceranoxide + ((1R,2R,4aS,8aS)-2,5,5,8a-tetramethyl-1-{2-[(1S,4aS,8aS)-5,5,8a-trimethyl-2-methylidenedecahydronaphthalen-1-yl]ethyl}decahydronaphthalen-2-ol
show the reaction diagram
-
the enzyme constructs the 6/6/6/6-tetracyclic scaffold baciterpenol A from the head-to-tail monocyclic tetraprenyl-betacurcumene as sesquarterpene cyclase, EC 4.2.1.137, and it also forms the 6/6/7/6/6-pentacyclic onoceranoxide and the 6/6 + 6/6-tetracyclic (1R,2R,4aS,8aS)-2,5,5,8a-tetramethyl-1-[2-[(1S,4aS,8aS)-5,5,8a-trimethyl-2-methylidenedecahydronaphthalen-1-yl]ethyl]decahydron from the tail-to-tail acyclic triterpene squalene via the 6/6-bicyclic intermediate 8alpha-hydroxypolypoda-13,17,21-triene
ratio 64:36
-
?
squalene
8alpha-hydroxypolypoda-13,17,21-triene
show the reaction diagram
-
-
intermediate product
-
?
additional information
?
-
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tetraprenyl-beta-curcumene cyclase from Bacillus megaterium is a bifunctional triterpene/sesquarterpene cyclase that converts head-to-tail tetraprenyl-beta-curcumene and tail-to-tail squalene into pentacyclic and bicyclic products, respectively, in vivo. BmeTC has an unprecedented catalytic function in cyclizing squalene from both termini and is an onoceroid synthase. The function of BmeTC enables the synthesis of (+)-ambrein
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APPLICATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
synthesis
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the onoceroid synthase function of BmeTC enables the synthesis of (+)-ambrein, a major constituent of ambergris that is difficult to obtain naturally, via a mutated squalene-hopene cyclase-catalyzed reaction from easily available squalene